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Isle of Wight

$125+ Cheap flights from Westchester County to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
1 adult, Economy
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Find flight deals from Westchester County to Isle of Wight

Cheapest flights from Westchester County to Isle of Wight
Explore the most affordable flight options available from Westchester County to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/105:19 pmHPN - ORF
1 stop4h 51mAmerican Airlines
dom. 12/145:08 amORF - HPN
1 stop4h 21mAmerican Airlines
Deal found 11/25$249
This American Airlines deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:30 amHPN - ORF
1 stop2h 58mAmerican Airlines
dom. 12/73:14 pmORF - HPN
1 stop4h 52mAmerican Airlines
Deal found 11/25$299
This Kiwi.com deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/101:14 pmHPN - ORF
2 stops18h 29mMultiple Airlines
dom. 12/147:15 amORF - HPN
1 stop13h 15mMultiple Airlines
Deal found 11/25$337
This American Airlines deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/125:19 pmHPN - ORF
1 stop4h 51mAmerican Airlines
dom. 12/216:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 11/24$338
This Kiwi.com deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/128:00 amHPN - ORF
2 stops23h 25mBreeze Airways
dom. 12/217:15 amORF - HPN
1 stop13h 15mBreeze Airways
Deal found 11/24$341
This American Airlines deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/311:29 amHPN - ORF
1 stop3h 15mAmerican Airlines
jue. 12/43:52 pmORF - HPN
1 stop6h 55mAmerican Airlines
Deal found 11/24$467
This American Airlines deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/2511:04 amHPN - ORF
2 stops21h 22mAmerican Airlines
vie. 1/26:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 11/24$476
This American Airlines deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/246:30 amHPN - ORF
1 stop11h 36mAmerican Airlines
mié. 12/316:00 amORF - HPN
1 stop4h 34mAmerican Airlines
Deal found 11/24$495
This Kiwi.com deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/278:00 amHPN - ORF
1 stop8h 03mBreeze Airways
sáb. 11/295:10 pmORF - HPN
2 stops18h 19mBreeze Airways
Deal found 11/25$536
This Gotogate deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/101:14 pmHPN - ORF
3 stops26h 49mBreeze Airways
dom. 12/147:15 amORF - HPN
1 stop13h 15mBreeze Airways
Deal found 11/25$546
This Gotogate deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:00 amHPN - ORF
2 stops23h 25mBreeze Airways
dom. 12/77:15 amORF - HPN
1 stop13h 15mBreeze Airways
Deal found 11/25$564

Cheap flight deals from Westchester County to Isle of Wight

Keep the following information in mind while searching for Westchester County to Isle of Wight flight deals. Data was last updated noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(American Airlines)

One-way from

$125
(CheapOair)

Popular in

March

Cheapest in

June

Average price

$247
Provider with most accurate pricing for New York (NYC)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Norfolk flights.
Search Deals
From Westchester County to Isle of Wight
Search Deals
One-way flight from Westchester County to Isle of Wight
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Isle of Wight that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated noviembre 26, 2025.
Use the filters below to find and compare flights from Westchester County to Isle of Wight that are best for you.

Fly from

Westchester County

Fly to

Isle of Wight

Route

Depart

Return

Price

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

vie. 1/9

10:00 am-2:36 pm

1 stop4h 36m

Norfolk

vie. 1/16

3:06 pm-8:08 pm

1 stop5h 02m

$213

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 2/15

11:00 am-2:03 pm

1 stop3h 03m

Norfolk

sáb. 2/21

5:00 am-9:29 am

1 stop4h 29m

$232

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

sáb. 1/31

10:00 am-2:11 pm

1 stop4h 11m

Norfolk

mar. 2/3

10:24 am-4:45 pm

1 stop6h 21m

$243

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

mié. 12/10

5:19 pm-10:10 pm

1 stop4h 51m

Norfolk

dom. 12/14

5:08 am-9:29 am

1 stop4h 21m

$249

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

vie. 12/12

5:19 pm-10:10 pm

1 stop4h 51m

Norfolk

dom. 12/21

6:00 am-10:34 am

1 stop4h 34m

$338

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

vie. 12/12

8:00 am-7:25 am

2 stops23h 25m

Norfolk

dom. 12/21

7:15 am-8:30 pm

1 stop13h 15m

$341

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

dom. 12/7

8:00 am-4:03 pm

1 stop8h 03m

$125

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

sáb. 4/25

5:07 pm-9:49 pm

1 stop4h 42m

$174

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

sáb. 1/10

8:15 am-4:35 pm

1 stop8h 20m

$177

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

jue. 4/23

6:22 am-11:06 am

1 stop4h 44m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 13 results
1
2

Best time to book a flight from Westchester County to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Westchester County with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Westchester County to Isle of Wight

What is the cheapest month to book a flight from Westchester County to Isle of Wight?

Currently, August is the cheapest month in which you can book a flight from Westchester County to Isle of Wight (average of $186). Flying from Westchester County to Isle of Wight in May is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from REU to I1W?

Find hourly flight availability from Westchester County to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 26, 2025.

It’s optimal to fly from Westchester County to Isle of Wight in the evening. By choosing this option you can save up to 42% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated noviembre 26, 2025.
Peruse reviews from past customers who have flown with American Airlines from Westchester County to Isle of Wight to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,038 reviews

Overall

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

Comfort

7.2

Crew

8.0

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Overall

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

Comfort

7.2

Crew

8.0

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Isle of Wight?

    Airlines like American Airlines fly from Westchester County to Isle of Wight in about 4h 36m. The time it takes to get you to your destination can typically vary by up to . Westchester County and Isle of Wight are separated by a distance of 318 mi.

  • What are the cheapest airlines to fly from Westchester County to Isle of Wight one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $125. However, be on the lookout for offers from American Airlines and JetBlue, as they are both options that can get you from Westchester County to Isle of Wight for a low price.

  • Can I find deals for flights from Westchester County to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Westchester County to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Isle of Wight.

  • Can I find deals for business class flights from Westchester County to Isle of Wight?

    Yes. Cheapflights offers flight deals from Westchester County to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Westchester County to Isle of Wight?

    Currently, August is the cheapest month in which you can book a flight from Westchester County to Isle of Wight (average of $186). Flying from Westchester County to Isle of Wight in May is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top airline flying from Westchester County to Isle of Wight

Discover the top airline that operate flights from Westchester County to Isle of Wight. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$198Average$453FlexibilityNo cancel feeOn-time71%

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